The Structure and Pitropic Rearrangement of the π-Complex of 1,2,3,3,4,5,6,6-Octamethyl-1,4-Hexadiene with Nitrosonium Cation

The Structure and Pitropic Rearrangement of the π-Complex of 1,2,3,3,4,5,6,6-Octamethyl-1,4-Hexadiene with Nitrosonium Cation Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 1997, Volume: 33, Number: 3, Pages: 317-324 Pages count : 8

Authors

Borodkin G.I. ¹ , Elanov I.R. ¹ , Shakirov M.M. ¹ , Shubin V.G. ¹

Affiliations

1	(Scopus) Novosibirsk Inst. of Organ. Chem., Siberian Division, Russian Academy of Sciences, pr. akademika Lavrent'eva 9, Novosibirsk, 630090, Russian Federation

By 1H and 13C NMR spectroscopy and the 27Al NMR isotope perturbation technique, it was found that interaction of 1,2,3,3,4,5,6,6-octamethyl-1,4-hexadiene with nitrosonium tetrachloroaluminate in SO2-CD2Cl2 or SO2-SO2ClF-CD2Cl2 gave a 2η-type π-complex that undergoes degenerate rearrangement via intramolecular and intermolecular migration of the NO group. The rate of intermolecular transfer of this group was greater in the SO2-CD2Cl2 than in the SO2-SO2ClF-CD2Cl2 system. Quantum-chemical MINDO/3 and MNDO/PM3 calculations on the complex of an NO+ cation with 1,4-cyclohexadiene and 1,2,3,3,4,5,6,6-octamethyl-1,4-hexadiene suggest that stability of the 2η π-complexes is higher than that of the corresponding σ-complexes or 4η π-complexes.

Borodkin G.I. , Elanov I.R. , Shakirov M.M. , Shubin V.G.
The Structure and Pitropic Rearrangement of the π-Complex of 1,2,3,3,4,5,6,6-Octamethyl-1,4-Hexadiene with Nitrosonium Cation
Russian Journal of Organic Chemistry. 1997. V.33. N3. P.317-324. Scopus РИНЦ

Borodkin G.I. , Elanov I.R. , Shakirov M.M. , Shubin V.G.
Structure and rearrangement of pi-complex of 1,2,3,3,4,5,6,6-octamethyl-1,4-cyclohexadiene with nitrosonium-cation
Журнал органической химии (RUSS J ORG CHEM+). 1997. V.33. N3. P.363-370. WOS

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